Polybromo tertiary amine

Abstract

N,N-Bis(polybromophenyl)organoamines are useful flame retardants which may be admixed with polymers to impart flame retardancy to the resulting compositions. Examples of such flame retardants include N,N-bis(2,4,6-tribromophenyl)methylamine, N,N-bis(2,4,6-tribromophenyl)ethylamine, N,N-bis(2,4,6-tribromophenyl)-allylamine, and N,N-bis(2,4,6-tribromophenyl)benzylamine.

We claim: 
     
       1. A compound represented by the structural formula: ##STR5## wherein: a. R' is hydrogen, alkyl, alkenyl, phenylalkyl or phenyl; and b. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10  are each independently hydrogen or a substituent, with the provisos that at least three of R 1 , R 2 , R 3 , R 4 , and R 5  are bromo and that at least three of R 6 , R 7 , R 8 , R 9 , and R 10  are bromo.   
     
     
       2. The compound of claim 1 wherein R 1  and R 10  are each bromo. 
     
     
       3. The compound of claim 1 wherein R 1 , R 3 , R 5 , R 6 , R 8 , and R 10  are each bromo. 
     
     
       4. The compound of claim 1 wherein R' is hydrogen, unsubstituted alkyl having from 1 to about 9 carbon atoms, unsubstituted alkenyl having from 2 to about 5 carbon atoms, unsubstituted phenylalkyl in which the alkyl portion contains from 1 to about 3 carbon atoms, or unsubstituted phenyl. 
     
     
       5. The compound of claim 1 wherein R' is vinyl. 
     
     
       6. The compound of claim 1 which is N,N-bis(2,4,6-tribromophenyl)allylamine. 
     
     
       7. The compound of claim 1 wherein R' is substituted alkyl having from 1 to about 9 carbon atoms, substituted alkenyl having from 2 to about 5 carbon atoms, substituted phenylalkyl in which the alkyl portion contains from 1 to about 3 carbon atoms, or substituted phenyl, and wherein each substituent of said substituted alkyl, said substituted alkenyl, said substituted phenylalkyl, and said substituted phenyl is a minor substituent. 
     
     
       8. The compound of claim 1 wherein R' is hydrogen, alkyl, phenylalkyl, or phenyl. 
     
     
       9. The compound of claim 8 wherein R 1  and R 10  are each bromo. 
     
     
       10. The compound of claim 8 wherein R 1 , R 3 , R 5 , R 6 , R 8 , and R 10  are each bromo. 
     
     
       11. The compound of claim 8 wherein R' is hydrogen, unsubstituted alkyl having from 1 to about 9 carbon atoms, unsubstituted phenylalkyl in which the alkyl portion contains from 1 to about 3 carbon atoms, or unsubstituted phenyl. 
     
     
       12. The compound of claim 8 wherein R' is hydrogen, methyl, or phenyl. 
     
     
       13. The compound of claim 8 wherein R' is substituted alkyl having from 1 to about 9 carbon atoms, substituted phenylalkyl in which the alkyl portion contains from 1 to about 3 carbon atoms, or substituted phenyl, and wherein each substituent of said substituted alkyl, said substituted phenylalkyl, and said substituted phenyl is a minor substituent. 
     
     
       14. The compound of claim 8 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10  are each independently hydrogen or bromo with the provisos that at least three of R 1 , R 2 , R 3 , R 4 , and R 5  are bromo and that at least three of R 6 , R 7 , R 8 , R 9 , and R 10  are bromo. 
     
     
       15. The compound of claim 14 wherein R' is hydrogen, unsubstituted alkyl having from 1 to about 9 carbon atoms, unsubstituted phenylalkyl in which the alkyl portion contains from 1 to about 3 carbon atoms, or unsubstituted phenyl. 
     
     
       16. The compound of claim 15 wherein R 1  and R 10  are each bromo. 
     
     
       17. The compound of claim 15 wherein R 1 , R 3 , R 5 , R 6 , R 8 , and R 10  are each bromo. 
     
     
       18. The compound of claim 14 which is N,N-bis(2,4,6-tribromophenyl)ethylamine. 
     
     
       19. The compound of claim 14 which is N,N-bis(2,4,6-tribromophenyl)benzylamine. 
     
     
       20. N,N-bis(2,4,6-tribromophenyl)methylamine. 
     
     
       21. A composition comprising thermoplastic or thermosetting polymer and compound represented by the structural formula: ##STR6## wherein: a. R' is hydrogen, alkyl, alkenyl, phenylalkyl or phenyl; and b. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10  are each independently hydrogen or a substituent, with the provisos that at least three of R 1 , R 2 , R 3 , R 4 , and that R 5  are bromo and that at least three of R 6 , R 7 , R 8 , R 9 , and R 10  are bromo.   
     
     
       22. The composition of claim 21 wherein said compound is N,N-bis(2,4,6-tribromophenyl)methylamine. 
     
     
       23. The composition of claim 21 wherein said compound is N,N-bis(2,4,6-tribromophenyl)ethylamine. 
     
     
       24. A composition comprising (1) acrylonitrile-butadiene-styrene graft polymer, polyethylene or polyester, and (2) compound represented by the structural formula: ##STR7## wherein: a. R' is hydrogen, alkyl, alkenyl, phenylalkyl or phenyl; and b. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7  R 8 , R 9 , and R 10  are each independently hydrogen or a substituent, with the provisos that at least three of R 1 , R 2 , R 3 , R 4  and that R 5  are bromo and that at least three of R 6 , R 7 , R 8 , and R 10  are bromo.